Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Abstract

An organic electroluminescence device of one or more embodiments includes a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer and a second electrode disposed on the electron transport region, wherein the first electrode and the second electrode each independently includes at least one selected among Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, Zn, compounds thereof, mixtures thereof, and oxides thereof, and the emission layer includes a polycyclic compound represented by Formula 1, thereby showing long life and high efficiency:

What is claimed is: 
     
       1. An organic electroluminescence device, comprising:
 a first electrode; 
 a hole transport region on the first electrode; 
 an emission layer on the hole transport region; 
 an electron transport region on the emission layer; and 
 a second electrode on the electron transport region; 
 wherein the first electrode and the second electrode each independently comprise at least one selected from among Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, In, Sn, Zn, compounds thereof, mixtures thereof, and oxides thereof, and 
 the emission layer comprises a polycyclic compound represented Formula 1: 
 
       
         
           
           
               
               
           
         
         wherein in Formula 1, 
         X 1  to X 3  are each independently O, S, Se or NAr 1 , 
         “m” and “n” are each independently an integer of 0 to 3, 
         “o” and “p” are each independently an integer of 0 to 4, 
         “q” is an integer of 0 to 5, 
         Ar 1  is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, 
         R 1  to R 6  are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, 
         X 4  is a substituted phenyl group, a substituted or unsubstituted aryl group of 7 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 ring-forming carbon atoms, or is represented by the following Formula 2: 
       
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 2, 
 Y is B, P, P═O, P═S, or N, 
 R 7  and R 8  are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, and 
 “a” and “b” are each independently an integer of 0 to 5. 
 
     
     
       2. The organic electroluminescence device of  claim 1 , wherein the emission layer is to emit delayed fluorescence. 
     
     
       3. The organic electroluminescence device of  claim 1 , wherein the emission layer is a delayed fluorescence emission layer comprising a first compound and a second compound, and
 the first compound comprises the polycyclic compound. 
 
     
     
       4. The organic electroluminescence device of  claim 1 , wherein the emission layer is a thermally activated delayed fluorescence emission layer to emit blue light. 
     
     
       5. The organic electroluminescence device of  claim 1 , wherein Formula 1 is represented by any one selected from among Formula 3-1 to Formula 3-5: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 3-1 to Formula 3-5, 
 X 3 , X 4 , R 1  to R 6 , and “m” to “q” are the same as defined in Formula 1. 
 
     
     
       6. The organic electroluminescence device of  claim 1 , wherein, in Formula 1, a sum of “m” and “n” is 1 or more, and at least one selected from among R 1  and R 2  is the substituted or unsubstituted amine group. 
     
     
       7. The organic electroluminescence device of  claim 1 , wherein Formula 1 is represented by Formula 4: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 4, 
 n′ is an integer of 0 to 2, 
 Ar 2  and Ar 3  are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and 
 X 1  to X 4 , R 1  to R 6 , “m” and “o” to “q” are the same as defined in Formula 1. 
 
     
     
       8. The organic electroluminescence device of  claim 7 , wherein Formula 4 is represented by Formula 5: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 5, 
 m′ is an integer of 0 to 2, 
 Ar 4  and Ar 5  are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and 
 X 1  to X 4 , R 1  to R 6 , Ar 2 , Ar 3 , n′, and “o” to “q” are the same as defined in Formulae 1 and 4. 
 
     
     
       9. The organic electroluminescence device of  claim 8 , wherein Ar 2  to Ar 5  are each independently represented by Formula 6: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 6, 
 Ra is a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, and 
 “i” is an integer of 0 to 5. 
 
     
     
       10. The organic electroluminescence device of  claim 1 , wherein Formula 1 is represented by Formula 7: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 7, 
 q′ is an integer of 0 to 5, 
 R 5 ′ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, and 
 X 1 , X 2 , X 4 , R 1  to R 6 , and “m” to “q” are the same as defined in Formula 1. 
 
     
     
       11. The organic electroluminescence device of  claim 8 , wherein Formula 5 is represented by Formula 8: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 8, 
 q′ is an integer of 0 to 5, 
 R 5 ′ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, and 
 X 1 , X 2 , X 4 , R 1  to R 6 , Ar 2  to Ar 5 , m′, n′, and “o” to “q” are the same as defined in Formulae 1, 4, and 5. 
 
     
     
       12. The organic electroluminescence device of  claim 1 , wherein Formula 2 is represented by any one selected from among Formulae 2-1, 2-2, and 2-4: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formulae 2-1, 2-2, and 2-4, 
 Z 1  is O, S, or NAr 6 , 
 Ar 6  is a phenyl group, 
 a′ and b′ are each independently an integer of 0 to 4, and 
 R 7 , R 8 , “a” and “b” are the same as defined in Formula 2. 
 
     
     
       13. The organic electroluminescence device of  claim 1 , wherein the polycyclic compound represented by Formula 1 is at least one selected from among compounds represented in Compound Group 1: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       14. A polycyclic compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein in Formula 1, 
         X 1  to X 3  are each independently O, S, Se or NAr 1 , 
         “m” and “n” are each independently an integer of 0 to 3, 
         “o” and “p” are each independently an integer of 0 to 4, 
         “q” is an integer of 0 to 5, 
         Ar 1  is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, 
         R 1  to R 6  are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, 
         X 4  is a substituted phenyl group, a substituted or unsubstituted aryl group of 7 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle of 2 to 30 ring-forming carbon atoms, or represented by Formula 2: 
       
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 2, 
 Y is B, P, P═O, P═S, or N, 
 R 7  and R 8  are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, and 
 “a” and “b” are each independently an integer of 0 to 5. 
 
     
     
       15. The polycyclic compound of  claim 14 , wherein Formula 1 is represented by any one selected from among Formula 3-1 to Formula 3-5: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 3-1 to Formula 3-5, 
 X 3 , X 4 , R 1  to R 6 , and “m” to “q” are the same as defined in Formula 1. 
 
     
     
       16. The polycyclic compound of  claim 14 , wherein Formula 1 is represented by Formula 4 or Formula 5: 
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 4 and Formula 5, 
 m′ and n′ are integers of 0 to 2, 
 Ar 2  to Ar 5  are each independently a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and 
 X 1  to X 4 , R 1  to R 6 , “m”, and “o” to “q” are the same as defined in Formula 1. 
 
     
     
       17. The polycyclic compound of  claim 16 , wherein Ar 2  to Ar 5  are each independently represented by Formula 6: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 6, 
 Ra is a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, and 
 “b” is an integer of 0 to 5. 
 
     
     
       18. The polycyclic compound of  claim 14 , wherein Formula 1 is represented by Formula 7: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formula 7, 
 q′ is an integer of 0 to 5, 
 R 5 ′ is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, and 
 X 1 , X 2 , X 4 , R 1  to R 6 , and “m” to “q” are the same as defined in Formula 1. 
 
     
     
       19. The polycyclic compound of  claim 14 , wherein Formula 2 is represented by any one selected from among Formulae 2-1, 2-2, and 2-4: 
       
         
           
           
               
               
           
         
       
       and
 wherein in Formulae 2-1, 2-2, and 2-4, 
 Z 1  is O, S, or NAr 6 , 
 Ar 6  is a phenyl group, 
 a′ and b′ are each independently an integer of 0 to 4, and 
 R 7 , R 8 , “a” and “b” are the same as defined in Formula 2. 
 
     
     
       20. The polycyclic compound of  claim 14 , wherein the polycyclic compound represented by Formula 1 is at least one selected among compounds represented in Compound Group 1: